More has been written about Tuscany than any of Italy's other regions and rightly so, for, in terms of its art and architecture, Tuscany enjoys what might be described as an embarrassment of riches.
In addition to such familiar gems as the cities of Siena, San Gimignano, Arezzo, Lucca and Pisa, the region is awash with picturesque medieval hill top towns. There are also isolated Romanesque churches, medieval castles and abbeys, Renaissance and Baroque villas and gardens, many of which I will be writing about in my guide.
And most places are situated in one of the most beautiful landscapes Italy has to offer, making the journey often as rewarding as the destination.
I agree with the assessment of the Blue Guide: 'for beauty and interest in Tuscany, Siena is rivalled only by Florence'. I shall, therefore, make that city my first port of call.
Please note: If a monument or museum is highlighted in red, please click on it for a link to the official website.
Siena
The beautifully preserved medieval city of Siena has, today, a population of about 60,000, which is only 10,000 more than it had at the height of its power, over 600 years ago. In the first half of the 14th century, Siena was one of the largest (and most prosperous) cities in Europe, on a par with London, and much bigger than Rome. But in 1348 all this came to an end when the plague struck. It has been estimated that up to half the population perished, bringing to an end the city's golden age.
The Piazza del Campo
Siena is a city of brick not of stone and it is the uniform use of brick as a building material that gives the city its particular sense of harmony. And nowhere can this be better seen than in the Piazza del Campo, one of the most beautiful squares in the whole of Italy.
The shape of the brick-paved piazza is unique and is often compared to a shell or fan. But the Sienese like to compare it to the Virgin’s cloak or holy mantle. This is where the world famous horse race, the Palio, is held, but more of that a little later. The square is overlooked by a magnificent bell tower, which soars to a height of 336 feet or 102 meters.
The tower was built between 1338 and 1348 by builders from Perugia and faced in brick. The castellated top was designed by Lippo Memmi, a Sienese artist, and faced in stone. The tower is known as ‘La Torre del Mangia’, after the nickname of its first bell ringer, Mangiaguadagni, literally, the eater of money. He acquired the curious nickname, on account of his tendency promptly to spend everything he earned. 
In an age when clocks were few and far between, the bell tower regulated the daily life of the community, reminding people when to work and to pray. At dawn it signalled the lifting of the curfew and the opening of the city gates. At midday it rang to signify the break for lunch and so on until the return of the curfew at the end of the day. The bell, itself, is called ‘Il sunto’, for it is dedicated to Maria Assunta, the Virgin of the Annunciation.
The Palazzo Pubblico
Flanking the bell tower stands the Palazzo Pubblico, the medieval seat of government, which dates back to the end of the 13th century. It still functions today as the city's town hall. Decorating the arch of every single window is the Balzana, the black and white emblem of Siena. The Palazzo Pubblico is well worth visiting, for it houses a fascinating series of 14th century frescoes by major artists of the Sienese school, such as Simone Martini and the brothers Ambrogio and Pietro Lorenzetti.
La Fonte Gaia
On the opposite side of the square is a public fountain known as 'La Fonte Gaia'. The fountain was built at the beginning of the 15th century by Jacopo della Quercia, a local sculptor. It is known as ‘La Fonte Gaia’, the joyful fountain, for its completion was greeted with immense joy. It was fed by an aqueduct over 40 miles or 25 kms in length, which predated the building of the fountain by about a century. 
Provision of water was always of the first importance in any flourishing urban community in medieval Italy. Siena had its own particular problems. It was not situated on or near a river. It drew its water from vast underground supplies, which fed a series of public fountains scattered around the city. The construction of private wells was strongly encouraged. As the city grew in size, demand soon outstripped supply.
The reliefs one now sees in place at the back of the fountain are rather poor replicas of Jacopo della Quercia's original sculptures which, suffering from the ravages of time, neglect and the elements, were removed in the 19th century to the safety of the nearby town hall.
Twice a year, on July 2nd and August 16th, the Piazza del Campo hosts the celebrated Palio, Italy's most famous horse race. This, however, is no ordinary horse race, it is a highly-charged outpouring of excitement and emotion. The race takes place in the early evening and is preceded by a procession lasting over 2 hours. With seemingly endless beating of drums and waving of flags, it is a colourful pageant full of posturing. For more details, see the article at the bottom of this page.
Throughout the middle ages, Siena was known as the city of bankers and of saints. It was one of the most important banking centres in Europe and the Monte dei Paschi di Siena, is, in fact, the oldest bank in the world.
Siena's most important saint was born on March 25th, 1347. Her name was Caterina Benincasa and at the age of 17, she entered the third order of the Dominicans, thereby becoming a tertiary and not a nun. This allowed her to continue living in the world, while not being wholly part of it. She soon developed a reputation as a mystic and in 1375 she received the stigmata, following in the path of St Francis of Assisi, a century and a half earlier.
In 1380 she died in Rome, aged only 33. Her body is buried in that city, but her head was removed and transferred to the city of her birth, where a special chapel, in the Dominican church of San Domenico, was built to house it. She was canonised in 1462 and is known as St Catherine of Siena to distinguish her from St Catherine of Alexandria. She shares with St Francis of Assisi the honour of being the patron saint of Italy. 
As you walk around the city, you will see, again and again, a reference to one of the legends surrounding the origin of Siena, in the form of an image of a she wolf suckling a pair of twins. You may be forgiven for thinking that they are the legendary figures, Romulus and Remus, but you would be wrong.
The twins are in fact supposed to be Senius and Ascius, the twin sons of Remus, himself the twin brother of Romulus, the legendary founder of Rome. If Romulus and Remus are the stuff of legend, Senius and Ascius are a pure fantasy fabricated by the Sienese to give their city the classical pedigree that it so desired.
The Cathedral
Decorated with the familiar 'zebra' bands of white and dark-green stone, Siena's Duomo is the oldest of the great Tuscan Gothic churches. The building history of the cathedral, spanning eight centuries, is one of the longest in Italy. Although work started in 1215, the mosaics were not finished until the 19th century, while the bronze doors were only completed at the beginning of the 20th century. 
Of all the treasures in the cathedral I would single out two: the 13th century pulpit by Nicola Pisano and the Piccolommini Library, frescoed at the beginning of the 16th century by Pinturricchio.
In the first half of the 14th century, after only a century of construction, Siena’s prosperity led to a demand for an even greater and more magnificent building. In 1339, the decision was taken to expand the cathedral to twice its size, in the hope of making it surpass, in size and magnificence, those of its neighbours, in particular Florence to the north and Orvieto to the south.
The existing cathedral would not be demolished, but would be incorporated into the fabric of the new cathedral. This was a remarkably ambitious project, but almost immediately it came up against problems: both economic and structural. The new building was inadequately supported and financed. And, following the catastrophic outbreak of the Black Death, in 1348, the authorities faced an additional problem, namely, the shortage of skilled craftsmen. The project was eventually abandoned and the skeleton of the new cathedral still stands as a testament to a glorious, but unrealised ambition.
Today, the building houses the Cathedral Museum, which is home to probably the greatest picture ever painted in Siena, Duccio's image of the Maesta.
Santa Maria della Scala 
Directly opposite the cathedral stands a rather ordinary looking brick building, which contains some extraordinary frescoes. The building once housed a hospital which, since its foundation in the 9th century, catered to the thousands of pilgrims who plied their way to and from Rome.
Until very recently, it still functioned as a hospital; today, however, it is a museum. The 14th century, Sala del Pellegrinaio, is decorated with a series of colourful and detailed frescoes from the 1440s.
The Baptistery.
To the east of the cathedral, at the bottom of a steep flight of steps, stands the Baptistery. The Gothic facade is so large and imposing that people may be forgiven for thinking that this is in fact the entrance to the cathedral.
The Baptistery dates back to the 14th century and houses a beautiful 15th century hexagonal font, which is decorated with six bronze reliefs. The reliefs are not the work of a single hand, but the combined effort of some of the greatest names in Italian sculpture. Donatello, Ghiberti and Jacopo della Quercia all contributed one or more panels. My favourite panel is the 'Feast of Herod' by Donatello, a powerful and ground-breaking achievement.
‘He who does not know the Palio, does not know Siena’.
Siena is home to the celebrated Palio, the most famous horse race in Italy. And yet the holding of a Palio is nothing special, many other towns up and down the peninsula hold one; it is just that Siena's Palio (in fact, there are two) has become famous throughout the world. Perhaps, this is because Siena's Palio is more than simply a race, it is a ritual, a rite of passage for the young men of the city. It generates feverish excitement and is taken very, very seriously. Although the actual race takes place only twice a year, on July 2nd and August 16th, preparations for it seem to go on all year round.
The city of Siena is divided into 17 parishes or contrade and it is these contrade who compete for the pallium, the painted silk banner which is awarded to the winner. The Sienese are passionately loyal to their contrada and often identify themselves in terms of their contrada first and their city second.
There is usually a visual reference to the contrada on the walls of buildings; each is identified by its own specific symbol, such as a goose, caterpillar or a hedgehog. Each contrada also has its own colours, heraldic symbol, motto and patron saint. 
To represent one’s contrada in the procession which precedes the race, is seen as the greatest of honours. Throughout the year, at various points in the city, one can see groups of young men and boys practising their drumming and flag waving. The amount of time and energy that is devoted to the Palio, and the immense importance that is attached to it, is almost incomprehensible to the outsider, even an Italian outsider.
The Palio, which dates back to the 11th century, was originally run (without riders) in a straight line, starting from outside the city walls and finishing in front of the old cathedral of St Boniface. The prize was a pallium (the Latin word for a piece of woollen cloth), hence the word Palio. By the end of the 16th century the races were being run (with riders) around the Piazza del Campo.
Although there are 17 contrade in the city, only 10 participate in each race. On the last Sunday of May, crowds wait in the piazza to see which 3 contrade will join the 7, who take place by right, having not participated the previous year. This important decision is made by the drawing of lots.
On June 29th and August 13th the horses are selected after a series of trial runs and rides. They are then marked with a number from one to ten and lined up in a closure in front of the Palazzo Communale. The draw takes place in full view of the public. The number of the horse is drawn from one urn and the name of the contrada from the other.
The horse is then taken into possession by the barberesco and taken to the contrada. The jockey is hired by the contrada itself. Rarely from Siena, he has the double task of either winning the race or, failing that, to make sure that the contrada’s rival doesn’t win. (Traditionally, each Contrada has a friend and foe).
Four days before the race, the piazza takes delivery of tons of sand, which will be used to turn the square into a racetrack. A series of six trial heats are then held to evaluate both the horse and the jockey. The fifth, known as the dress rehearsal (which takes place on the day before the actual Palio) is also the occasion for a dinner, which is held in each contrada, even those not participating in the race. This is a time of promises and hopes of wishes and prayers of toasts, invocations to the Madonna and to their patron saint. The last, the provaccia, takes place on the morning of the actual Palio.
The race, which takes place in the evening, at 7.30pm, is preceded by an colourful and exciting corteo storico (historical procession), in which all 17 contrade take part. The procession takes about two hours to weave its way into and around the piazza.
The start of the race (the mossa) is governed by a complex series of actions. An invalid start is announced by a mortaretto, an explosive charge.The actual race is over in an instant or, at least, it seems to be. But so much emotion and excitement is squeezed into the seventy-five seconds, which, on average, it takes a horse to complete the three laps of the piazza. It is impossible to remain unaffected by the atmosphere. The tension builds up as the evening progresses and completely explodes when the drum roll announces the start of the actual race.
The jockeys must go round the Piazza three times (a distance of almost one kilometre). They may block other riders, but are not allowed to grab one another. Unlike modern horse races, in the Palio a horse may win even if it has lost its rider. The finish of the race is signalled by a drum roll and the firing of the mortaretto. At this point, the members of the winning contrada give full voice to their joy.
